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Financial Management, Tailored


We serve retirees, business owners, and nonprofit organizations with disciplined advice, mission-aligned portfolios, and thoughtfully
crafted strategies that reflect their goals, values, and long-term vision.

Sound Plans Start at the Source

“Ideas, like large rivers, never have just one source. Just as the waters of a river near its mouth are composed largely of the waters of many tributaries, so an idea, in its final form, is composed largely of later additions.”  - Willy Ley, Science Writer

This belief is foundational to Headwater. No single source has all the answers, which is why the ideas behind your plan are shaped by a broad network of expertise. Led by a former CPA with more than 25 years in the financial services industry, the firm combines proprietary market research with access to specialized planning resources and trusted relationships with market strategists, CPAs, and estate attorneys. Like a river that gathers strength along its course, your plan continues to evolve as your life, goals, and market conditions change.

Integrating these insights requires discipline and foresight. Pursuing meaningful outcomes means thinking creatively, anticipating challenges, and positioning yourself for opportunities that lie ahead. 


An Open Letter to Our Visitors
Before becoming a financial advisor, Mike sat on the other side of the table. Here’s what that taught him, and why he built Headwater differently.

Who We Serve

Individuals & families

Individuals & families

We help individuals and families create wealth around what matters most to them, focusing on the things we can control: a clear financial plan, thoughtful investment management, and estate planning that protects the people they love.

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Business Owners

Business Owners

We help business owners create wealth around what matters most to them, focusing on the things we can control: stewarding company assets and creating retirement solutions for the team they’ve built.

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Non-Profits

Non-Profits

We help non-profit organizations grow their resources around their mission, focusing on the things we can control: prudent investment oversight and a financial strategy that supports lasting impact.

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Why we Serve

Behind every plan is a person and a story.

James Stennett

I first met Mike Caputo 25 years ago in the depths of the DotCom Bubble. At the time, I was invested through with a large national firm that told me "we just need to ride it out." Mike took my portfolio and not only stopped the bleeding, but got me back on a positive track. Over the years since, he has been an astute and trusted advisor through the various changes in the markets.

Carla Nesbitt

My life changed forever with the sudden passing of my beloved husband, Doug.  Not only was I dealing with the grief of his loss, but all the financials that came with it.  Mike Caputo has not only navigated that for me, but he is so much more than a financial advisor.  He has been there for me every step of the way. If I have a question about ANYTHING, he will get that answer for me and help me with a solution.  


I truly don't know how I would have gone through this process without him.  He has given me so much peace of mind and I am so grateful. 

James Pickering, Attorney

I’ve worked with Mike for over 20 years, and I’ve been very pleased with him throughout this time.  He’s a true professional and a thoughtful strategic planner who always keeps my best interests at heart. I trust him completely and feel comfortable confiding in him about my financial goals and concerns.


What I appreciate most is that he listens. When I bring him my own investment ideas, he takes the time to talk them through and explain what’s likely to work and what isn’t. He’s always available to discuss my options and where things are heading, and he consistently goes an extra ten miles.


I've met his family on several occasions. Being a family man and understanding what really matters, comes through in how he treats his clients. I’m very satisfied with how he runs his business and grateful for the guidance he’s given me over the years.
Here to Serve

Here to Serve

We believe true wealth is measured not only by financial success, but by the ability to live with purpose, provide for those you love, and leave a lasting impact. Our role is to serve as a trusted guide, helping you make thoughtful decisions with clarity and confidence so your financial resources can support the life, legacy and values that matter most.

Let's have a conversation

Whether you prefer to meet in person or connect by phone, we would welcome the opportunity to learn more about you. We offer a brief introductory conversation at no cost or obligation. We look forward to connecting!

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Take Charge of Your 401(k)

Keep up with your financial needs while avoiding common (and expensive) rollover mistakes. We put together this guide to help you avoid these critical mistakes and potentially save you thousands in taxes and fees.